Benzene-1,3-disulfonyl Fluoride Mediated Synthesis of Glycosyl Fluorides from Glycosyl Hemiacetals

We developed an efficient method for synthesizing glycosyl fluorides from glycosyl hemiacetals using benzene-1,3-disulfonyl fluoride (<b>S2</b>) as the fluorinating agent in combination with the base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) under mild conditions. This approach enabled the successful synthesis of 17 glycosyl fluorides with various functional groups, including disaccharides and deoxysulfates, with yields of up to 99%. The utility of these synthesized glycosyl fluorides was further demonstrated in the synthesis of important <i>O</i>- and <i>C</i>-glycosides.